1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → 2-(2-imidazolin-2-yl)-1-phenyl-1H-indole

HRID 1770121Notes

Reaction equation

HRID 1770121 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]#[N:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:29](N)[CH2:30][NH2:31]>>[NH:17]1[CH2:29][CH2:30][N:31]=[C:16]1[C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

3

Reactant 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 20095505HCID 20095505, compound

Product 1

HCID 102208542-(2-imidazolin-2-yl)-1-phenyl-1H-indole

Conditions

Temperature
200 °C

Procedure

A stirred mixture of 1-phenyl-1H-indole-2-carbonitrile (15 g) and ethylenediamine monotosylate (17.6 g) was heated at 200° C. for 2 hours. After cooling, the reaction mixture was partitioned between toluene (100 ml) and dilute hydrochloric acid (400 ml). The aqueous layer was extracted with diethyl ether, cooled in an ice bath then basified with concentrated ammonia and reextracted with dichloromethane. The combined dichloromethane extracts were washed with water, dried and the solvent removed in vacuo. The residue was purified by chromatography on neutral alumina (grade III) eluting with 1% methanol in dichloromethane, followed by trituration with toluene to give 2-(2-imidazolin-2-yl)-1-phenyl-1H-indole as a white solid: yield 16.6 g (90%); mp 180.5°-182° C. The hydrochloride salt was prepared as described above: yield 16.3 g (95%); mp 263.5°-265.5° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between toluene (100 ml) and dilute hydrochloric acid (400 ml)
  3. extractionThe aqueous layer was extracted with diethyl ether
  4. temperaturecooled in an ice bath
  5. washThe combined dichloromethane extracts were washed with water
  6. customdried
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by chromatography on neutral alumina (grade III)
  9. washeluting with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-3e801975a1254b6baff85c21d1498fbe
Source dataset
uspto-grants-1995_01
Patent number
US05385919

Reaction notes

Loading…